Multivalent neoglycoconjugates: solid-phase synthesis of N-linked α-sialodendrimers

Abstract

A series of N-linked α-sialodendrimers with valencies of 2, 4 and 8 has been scaffolded on an N,N-bis(3-aminopropyl)succinamic acid core using Wang resin and 9-fluorenylmethoxycarbonyl and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate solid-phase chemistry.

References

1. D. Astruc, C. R. Acad. Sci. Paris, 1996, 322, 757.
2. D. A. Tomalia and H. D. Durst, Top. Curr. Chem., 1993, 165, 193.
3. C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 1990, 112, 7638.
4. T. Kawaguchi, K. L. Walter, C. L. Wilkins and J. S. Moore, J. Am. Chem. Soc., 1995, 117, 2159.
5. S. C. Zimmerman, F. W. Zeng, D. E. G. Reichert and S. V. Kolotuchin, Science, 1996, 271, 1095.
6. J. P. Tam, Proc. Natl. Acad. Sci. USA, 1988, 85, 5409.
7. R. Roy, Polym. News., 1996, 21, 226; R. Roy, Top. Curr. Chem., 1997, 187, 241; K. Aoi, K. Itoh and M. Okada, Macromolecules, 1995, 28, 5391 and references therein.
8. E. J. Toone, Curr. Opin. Struct. Biol., 1994, 4, 719.
9. R. Roy, Curr. Opin. Struct. Biol., 1996, 6, 692 and references cited therein.
10. R. Roy, D. Zanini, S. J. Meunier and A. Romanoska, J. Chem. Soc., Chem. Commun., 1993, 1862.
11. J. C. Paulson, in The Receptors, ed. M. Conn, Academic Press, Orlando, 1985, vol. 2, p. 131.
12. D. Zanini and R. Roy, J. Org. Chem., 1996, 61, 7348.
13. D. Zanini and R. Roy, J. Am. Chem. Soc., 1997, 119, 2088.
14. S.-I. Murahashi, T. Naota and N. Nakajima, Chem. Lett., 1987, 879.
15. E. Kaiser, R. L. Colescott, C. D. Bossinger and P. I. Cook, Anal. Biochem., 1971, 34, 595.
16. F. Tropper, F. O. Andersson, S. Braun and R. Roy, Synthesis, 1992, 618.